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(±)-dihydromint lactone
(±)-Dihydromint lactone is a lactonic compound used as a flavor and fragrance ingredient with minty, coconut, and coumarinic notes.
General Material Description
(±)-Dihydromint lactone, known chemically as 3,6-dimethylhexahydrobenzofuran-2(3H)-one, is a bicyclic lactone characterized by the molecular formula C10H16O2. This compound presents as a clear liquid and is recognized for its distinctive odor profile combining lactonic, minty, coumarinic, and tonka bean-like notes, making it valuable in flavor and fragrance applications. It is also commonly referred to as koumalactone among other synonyms. This lactone is typically synthesized for commercial use, derived through methods involving the hexahydrobenzofuran framework. Its chemical structure includes a fused ring system with a γ-lactone moiety, contributing to its sensory properties. The compound links to controlled vocabulary entries such as PubChem CID 53436632, which provides detailed chemical and safety data.
Occurrence, Applicability & Potential Uses
(±)-Dihydromint lactone occurs naturally in certain plant-derived materials, though it is primarily obtained via synthesis for commercial applications. Its biological occurrence is related to derivatives of cyclohexylacetolactones. This compound finds application as a flavor and fragrance agent due to its medium-strength tonka bean-like aroma and lactonic, minty qualities. It is widely used in formulations targeting yellow fruit flavors such as mango, pineapple, and peach, and complements tea and mint flavor profiles effectively. Additionally, it enhances sensory notes in products like chocolate, dairy, nut, tropical, and whiskey flavors. The compound is incorporated in perfumery for accords associated with floral, woody, powdery, and oriental scents. Its use levels and safety evaluations are governed by standards such as FEMA (US) and IFRA (Global), ensuring compliance in food and fragrance products.
Physico-Chemical Properties Summary
(±)-Dihydromint lactone exhibits physicochemical characteristics which influence its formulation and application. It is a moderately lipophilic compound with a logP value of approximately 2.14, indicating moderate solubility in nonpolar solvents and compatibility with alcohols. Its specific gravity at 20 °C ranges from 1.016 to 1.022, and it has a refractive index between 1.464 and 1.47 at the same temperature. The boiling point lies around 274 to 276 °C at atmospheric pressure. The compound has a low vapor pressure of 0.007 mmHg at 25 °C, implying moderate volatility that supports its persistence in fragrance compositions. It is soluble in alcohol and moderately soluble in water, with an experimentally determined solubility of 2.70 g/L at 20 °C. The flash point is reported near 107 °C, denoting relative thermal stability during typical handling and formulation processes. Stability data suggest low volatility and compatibility with various product matrices including detergents, fine fragrances, shampoos, and shower gels at trace levels. These properties facilitate its use in both flavor and fragrance industries with sustained substantivity.
FAQ
What is (±)-dihydromint lactone and what are its main characteristics?
(±)-Dihydromint lactone is a bicyclic lactone compound known for its distinct lactonic and minty aroma, often described as coumarinic with tonka bean and tobacco undertones. Chemically named 3,6-dimethylhexahydrobenzofuran-2(3H)-one, it has the molecular formula C10H16O2. This compound is valued in the flavor and fragrance industries for its medium-strength tonka-like odor and its ability to enhance fruity notes such as mango and pineapple. It is typically synthesized for use rather than extracted directly from natural sources. Its structural features include a fused ring lactone, which contributes to its olfactory profile and physicochemical behavior.
How is (±)-dihydromint lactone used and in what types of products can it be found?
(±)-Dihydromint lactone is primarily used as a flavor and fragrance ingredient. Its applications include enhancing yellow fruit flavors like mango, pineapple, and peach, as well as mint and tea-like notes. The compound contributes to various food flavor categories such as chocolate, dairy, nut, tropical, and whiskey flavors. In perfumery, it is incorporated to add tonka bean-like, floral, woody, and oriental nuances. Its moderate volatility and solubility profile allow formulation in diverse product forms including baked goods, beverages, confectionery, and cosmetic items like shampoos and soaps, often at the trace to low percent levels recommended by industry standards.
What safety and regulatory considerations exist for (±)-dihydromint lactone usage?
(±)-Dihydromint lactone has been evaluated for safety by regulatory bodies including FEMA (US) and IFRA (Global). It is classified in structure class III by the RIFM assessment and is considered safe for use in fragrance concentrates up to 1.0000% according to IFRA guidelines. Its Maximised Survey-derived Daily Intakes (MSDI) vary by region, with 8.00 μg/capita/day in the EU and 12.00 μg/capita/day in the USA. Toxicology data do not indicate significant hazards under normal use conditions, and no GHS hazard classifications are assigned. Extensive safety reviews and usage limitations can be referenced through FEMA and IFRA publications. The compound is listed as FEMA GRAS for flavor use, ensuring its acceptance for use in food applications within regulated limits.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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Other Information
| (IUPAC): | Atomic Weights of the Elements 2011 (pdf) |
| Videos: | The Periodic Table of Videos |
| tgsc: | Atomic Weights use for this web site |
| (IUPAC): | Periodic Table of the Elements |
| FDA Substances Added to Food (formerly EAFUS): | View |
| HMDB (The Human Metabolome Database): | HMDB32219 |
| FooDB: | FDB009289 |
| ChemSpider: | View |
| EFSA Update of results on the monitoring of furan levels in food: | Read Report |
| EFSA Previous report: Results on the monitoring of furan levels in food: | Read Report |
| EFSA Report of the CONTAM Panel on provisional findings on furan in food: | Read Report |
General Material Information
| Preferred name | (±)-dihydromint lactone |
| Trivial Name | 3,6-Dimethylhexahydrobenzofuran-2(3H)-one |
| Short Description | koumalactone (Firmenich) |
| Formula | C10 H16 O2 |
| CAS Number | 92015-65-1 |
| FEMA Number | 4032 |
| Flavis Number | 10.05 |
| FDA UNII | V49A09DWAA |
| COE Number | 1005 |
| NMR Predictor | External link |
| JECFA Food Flavoring | 1161 dihydromintlactone |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 92015-65-1 ; (+/-)-DIHYDROMINTLACTONE |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 168.2359161377 |
| Specific gravity | @ 20 °C |
| Pounds per Gallon | 8.464 to 8.514 |
| Refractive Index | 1.464 to 1.47 @ 20 °C |
| Boiling Point | 274 to 276°C @ 760 mm Hg |
| Acid Value | 1 max KOH/g |
| Vapor Pressure | 0.007 mmHg @ 25 °C |
| Flash Point TCC Value | 107.22 °C TCC |
| logP (o/w) | 2.14 |
| Solubility | |
| alcohol | Yes |
| water, 2.70 g/L at 20 °C (exp) | Yes |
| Stability | |
| APC: traces - 0.5% | Unspecified |
| candle: traces - 1% | Unspecified |
| detergent: traces - 0.5% | Unspecified |
| fine fragrances: traces - 0.5% | Unspecified |
| shampoo: traces - 0.5% | Unspecified |
| shower gel: traces - 0.5% | Unspecified |
| soap: traces - 0.5% | Unspecified |
| softener: traces - 0.5% | Unspecified |
Organoleptic Properties
| Odor Type: Tonka | |
| coumarinic, lactonic, tonka, phenolic, tobacco, gourmand | |
| Odor strength | medium , recommend smelling in a 10.00 % solution or less |
| Substantivity | 168 hour(s) at 10.00 % |
| General comment | At 10.00 % in dipropylene glycol. coumarinic lactonic tonka phenolic tobacco gourmand |
| Flavor Type: Lactonic | |
| lactonic, coconut, coumarinic, minty, fruity, herbal | |
| General comment | Lactonic, coconut, coumarinic, minty, fruity and herbal notes |
| NATACTONE ® can be widely applied in fruit flavors where lactones are used. It gives great effect to yellow fruit flavors such as mango pineapple and peach. Its coumarinic and minty twist is perfect for tea and mint flavors. | Lactonic coconut coumarinic minty fruity and herbal notes |
Potential Uses
| Applications | |
| Odor purposes | Acacia , Allspice , Amber , Baby powder , Balsam , Castoreum , Cedar forest , Cinnamon , Clover , Coconut , Cream , Fir balsam , Floral , Graham cracker , Hawthorn , Hay new mown hay , Herbal , Mint , Moss , Musk , Oriental , Powder , Tobacco , Tonka bean , Tonka bean , Vanilla , Woody |
| Flavoring purposes | Chocolate cacao , Dairy , Nut , Tropical , Whiskey |
| Other purposes | Autumn leaf |
Safety Information
Safety information
| Hazards identification | |
| Classification of the substance or mixture | |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) | |
| None found. | |
| GHS Label elements, including precautionary statements | |
| Pictogram | |
| Hazard statement(s) | |
| None found. | |
| Precautionary statement(s) | |
| None found. | |
| Oral/Parenteral Toxicity: | |
| Not determined | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| flavor and fragrance agents | |||
| RIFM Fragrance Material Safety Assessment: Search | |||
| IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice | |||
| Recommendation for (±)-dihydromint lactone usage levels up to: | |||
| 1.0000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 8.00 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 12.00 (μg/capita/day) | ||
| Structure Class: | III | ||
| Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS). | |||
| The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library | |||
| publication number: 21 | |||
| Click here to view publication 21 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | 1.00000 | 3.00000 | |
| beverages(nonalcoholic): | 1.00000 | 3.00000 | |
| beverages(alcoholic): | 0.30000 | 1.00000 | |
| breakfast cereal: | 0.30000 | 1.00000 | |
| cheese: | - | - | |
| chewing gum: | 3.00000 | 10.00000 | |
| condiments / relishes: | - | - | |
| confectionery froastings: | 0.30000 | 1.00000 | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | 1.00000 | 3.00000 | |
| fruit ices: | 0.30000 | 1.00000 | |
| gelatins / puddings: | 0.50000 | 2.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | 1.00000 | 3.00000 | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | - | - | |
| milk products: | 0.30000 | 1.00000 | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | 0.30000 | 1.00000 | |
| soups: | - | - | |
| sugar substitutes: | - | - | |
| sweet sauces: | - | - | |
Safety references
| European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies... |
| European Food Safety Authority (EFSA) reference(s): |
| Flavouring Group Evaluation 80 (FGE.80) - Consideration of alicyclic, alicyclic-fused and aromatic-fused ring lactones evaluated by JECFA (61st meeting) structurally related to a aromatic lactone evaluated by EFSA in FGE.27 (2008) View page or View pdf |
| Flavouring Group Evaluation 80, Revision 1 (FGE.80Rev1): Consideration of alicyclic, alicyclic-fused and aromatic-fused ring lactones evaluated by JECFA (61st meeting) structurally related to a aromatic lactone evaluated by EFSA in FGE.27 (2008) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 96 (FGE.96): Consideration of 88 flavouring substances considered by EFSA for which EU production volumes / anticipated production volumes have been submitted on request by DG SANCO. Addendum to FGE. 51, 52, 53, 54, 56, 58, 61, 62, 63, 64, 68, 69, 70, 71, 73, 76, 77, 79, 80, 83, 84, 85 and 87. View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):92015-65-1 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :53436632 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:2 |
| 3,6-dimethyl-3a,4,5,6,7,7a-hexahydro-3H-benzofuran-2-one |
| Chemidplus:0092015651 |